Organocatalyzed Michael addition of acetone to β-nitrostyrenea.
| ||||
|---|---|---|---|---|
| Entry | Cat | T | % convb | e. r.c |
| 1 | 4 | NO | <5 | — |
| 2 | 6a | NO | 55 | 57 : 43 |
| 3 | 6b | NO | 28 | 54 : 46 |
| 4 | 4 | YES | 17 | 57 : 43 |
| 5 | 6a | YES | 85 | 78 : 22 |
| 6 | 6b | YES | 95 | 91 : 9 |
| 7 | — | YES | 0 | 0 |
Reaction conditions: acetone (0.25 mmol), β-nitrostyrene (0.025 mmol), catalyst (10 mol%), N-hexylthymine (0 or 0.125 mmol), CH2Cl2 (100 μL), 25 °C, 5 days.
Determined by 1H NMR from the crude reaction.
e. r. determined by HPLC using a Daicel ChiralPak AS-H column.